N-Succinimidyl 11-(maleimido)undecanoate

 CAS No.: 87981-04-2  Cat No.: BP-500566  Purity: 95% 4.5  

N-Succinimidyl 11-(maleimido)undecanoate is a heterobifunctional, amine-reactive NHS-ester and thiol-reactive maleimide linker designed for modular PROTAC assembly. Structurally, it contains an eleven-carbon flexible spacer that spatially separates the two reactive termini, enabling controlled conjugation without requiring rigid scaffolds. In PROTAC workflows, the NHS ester can be used to label primary amines on one component (e.g., a ligand bearing a lysine or amino group), forming a stable amide linkage, while the maleimide reacts selectively with cysteine thiols on a second component to generate a thioether bond. This orthogonal reactivity supports efficient, sequential coupling strategies that preserve functional groups and can be used to tune effective distance and orientation between the target-binding and E3-ligase-binding domains. The linker’s flexible chain and chemoselective conjugation make it valuable for constructing well-defined targeted protein degradation reagents and for optimizing linker length effects on ternary complex formation and degradation potency.

N-Succinimidyl 11-(maleimido)undecanoate

Structure of 87981-04-2

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PROTAC Linker
Molecular Formula
C19H26N2O6
Molecular Weight
378.42
Appearance
White Powder

* For research and manufacturing use only. Not for human or clinical use.

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Purity
95%
Appearance
White Powder
Storage
2-8 °C
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
(2,5-dioxopyrrolidin-1-yl) 11-(2,5-dioxopyrrol-1-yl)undecanoate
Synonyms
KMUS; Maleimide-C10-NHS ester; N-Succinimidyl 11-maleimidoundecanoate; 11-Maleimidoundecanoic Acid N-Succinimidyl Ester; 2,5-dioxopyrrolidin-1-yl 11-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)undecanoate; Maleimide-(CH2)10-COONHS; 11-Maleimidoundecanoicacid-NHS; 11-(Maleimido)undecanoic acid N-succinimidyl ester; VZ21668; 11-Maleimidoundecanoic acid-NHS (KMUS); 2,5-Dioxo-3-pyrroline-1-undecanoic acid succinimidyl ester
Boiling Point
520.4±42.0 °C (Predicted)
Melting Point
90-94 °C
Density
1.250±0.10 g/cm3 (Predicted)
InChI Key
SGNVTRHWJGTNKV-UHFFFAOYSA-N
InChI
InChI=1S/C19H26N2O6/c22-15-10-11-16(23)20(15)14-8-6-4-2-1-3-5-7-9-19(26)27-21-17(24)12-13-18(21)25/h10-11H,1-9,12-14H2
SMILES
C1CC(=O)N(C1=O)OC(=O)CCCCCCCCCCN2C(=O)C=CC2=O

N-Succinimidyl 11-(maleimido)undecanoate is a bifunctional PROTAC linker designed to connect amine-bearing ligands to thiol-reactive moieties, enabling modular assembly of targeted protein degraders. Its dual-reactivity supports efficient conjugation workflows and allows researchers to tune linker placement to influence ternary complex formation and degradation performance. The subsequent points describe the linker’s structure and practical reactivity considerations for PROTAC construction in detail below.

Structure: The linker contains an N-hydroxysuccinimide ester for amine coupling and a terminal maleimide for selective thio-Michael addition. It features a flexible aliphatic spacer that provides conformational reach, with stable amide and ester functionalities that support controlled, stepwise conjugation.

Reactivity: Use the NHS-ester under mildly basic aqueous conditions to acylate primary amines on one PROTAC component, typically with buffered solvent systems and controlled temperature to minimize hydrolysis. After purification or in a sequential one-pot strategy, introduce thiol-bearing partners to enable maleimide-thio-Michael addition. Avoid excess free thiols and strongly nucleophilic additives that can compete with maleimide reactivity; inert handling and timely reaction setup improve coupling efficiency.

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* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
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Historical Records: Succinimidyl 2-([4,4'-azipentanamido]ethyl)-1,3'-dithioproprionate | 3-(4-methoxy-3-oxo-1H-isoindol-2-yl)piperidine-2,6-dione | Diazo Biotin-PEG3-alkyne | 2,5,8,11,14,17-Hexaoxa-19-nonadecanyl Methanesulfonate | Succinimidyl 6-(4,4'-azipentanamido)hexanoate | Bis-(m-PEG8-amido)-hexanoic acid | (2S,4R)-1-[(2S)-2-acetamido-3-methylbutanoyl]-4-hydroxy-N-[(1S)-3-(methylamino)-3-oxo-1-phenylpropyl]pyrrolidine-2-carboxamide | XY-06-007 | (2S,4R)-4-hydroxy-N-[(1S)-3-(methylamino)-1-[4-(4-methyl-1,3-thiazol-5-yl)phenyl]-3-oxopropyl]-1-[(2R)-3-methyl-2-(3-methyl-1,2-oxazol-5-yl)butanoyl]pyrrolidine-2-carboxamide | Phosphonic acid,1,4-butanediylbis-, tetraethyl ester (9CI) | N-Succinimidyl 11-(maleimido)undecanoate

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